For many years since its cancellation the show has been the subject of an unusual urban legend involving a 17th unaired episode. The episode, entitled "Lenny's Bicycle Built For Two", guest starred legendary Boston comedy personality Rob Marco Jr. in the role of Lenny's nephew, and the late Gordon Jump reprising his role as the bicycle shop owner from Diff'rent Strokes. The plot was rumored to involve a drunk Lenny accidentally leaving Rob behind at the bicycle shop. When Lenny sobers up he returns to the shop to find Rob has been molested repeatedly by the shop owner. Lenny then beats the shop owner to death with a bicycle pump, and (in a fit of bloodlust) beats Rob to death as well. ABC deemed the episode "too extreme" for tv and the censors refused to air it. It's believed that copies of the episode were destroyed, save one that is believed to be in the possession of tape tarder John McAdam. When asked about the episode on an infomercial for dietary fiber supplements, Lenny claimed to have no recollection of shooting it, adding "I used a lot of hallucinogenic drugs back then." To date the episode has never been seen publicly.

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Lenny starred long-time Boston stand-up comedianLenny Clarke as Lenny Callahan, a working-class Bostonian who held down two jobs, a daytime one as laborer for the local electric utility and an evening one as a doorman at a posh hotel. His wife, Shelley (Lee Garlington) was a full-time homemaker and the couple had three children (presumably the reason Lenny needed to keep two jobs). One of their daughters, Kelly, was played by Jenna von Oÿ. Daughter Tracy was played by Alexis Caldwell. Other characters included Lenny's brother Eddie (Peter Dobson), a get-rich-quick schemer, and their parents, Pat (Eugene Roche) and Mary (Alice Drummond).

Initially scheduled against two established programs, the Top 30 show The Wonder Years on ABC and the Top 20 hit Unsolved Mysteries on NBC, Lenny was a ratings failure and put on hiatus in October. It was brought back in a new time slot in December, but cancelled permanently in March 1991.